(+/-)-2-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one

ID: ALA457386

Cas Number: 23520-34-5

PubChem CID: 322636

Max Phase: Preclinical

Molecular Formula: C8H7NO3

Molecular Weight: 165.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2ccccc2OC1O

Standard InChI:  InChI=1S/C8H7NO3/c10-7-8(11)12-6-4-2-1-3-5(6)9-7/h1-4,8,11H,(H,9,10)

Standard InChI Key:  VMQBFYRBJKDACN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 12 13  0  0  0  0  0  0  0  0999 V2000
   -4.0755  -16.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0766  -17.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570  -17.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588  -16.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6471  -16.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469  -17.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308  -17.9730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169  -16.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312  -16.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955  -16.3239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176  -17.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024  -17.9720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  6  2  0
  1  2  2  0
  5  4  2  0
  6  7  1  0
  8  9  1  0
  9  5  1  0
  4  1  1  0
  8 10  1  0
  5  6  1  0
  7 11  1  0
  8 11  1  0
 11 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA457386

   2-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 165.15

Molecular Weight (Monoisotopic): 165.0426

AlogP: 0.34

#Rotatable Bonds: ┄

Polar Surface Area: 58.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: ┄

CX LogP: 0.47

CX LogD: 0.46

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.58

Np Likeness Score: 1.06

References

1. Otsuka H, Hirai Y, Nagao T, Yamasaki K..  (1988)  Anti-inflammatory activity of benzoxazinoids from roots of Coix lachryma-jobi var. ma-yuen.,  51  (1): [PMID:2453615] [10.1021/np50055a009]

2. Bravo HR, Copaja SV, Argandoña VH..  (2004)  Chemical basis for the antifeedant activity of natural hydroxamic acids and related compounds.,  52  (9): [PMID:15113164] [10.1021/jf030766t]

Source

Source(1):

• Scientific Literature